Fall brings reds, oranges, yellows, and purples; there’s no one color to represent Autumn. Likewise, this year I thought that a single (or even two or three) Fall flavor(s) in a cupcake would not do. I decided to combine some past single-flavor Fall cupcake favorites into one Everything Fall Cupcake recipe. What you see above are (take a deep breath) pumpkin, spiced rum, and maple cupcakes topped with cinnamon cream cheese frosting and dried cranberries – with brown sugar frosting-topped apple cobbler cupcakes baked inside.

While I admire many food blogs for their tempting recipes, personable and descriptive writing, and mouthwatering food photography, I am most impressed with blogs that show creativity. Jessie Oleson (CakeSpy) has one of the most creative blogs out there. She combines her so-cute-you-want-to-pinch-them cartoons – featuring the now famous (in the cupcake world) cupcake character, Cuppie – with over-the-top recipes that always make me wonder why no one thought of them before.

Although I haven’t met Jessie, we’ve emailed and tweeted over the years and she was a judge in this year’s Ice Cream Cupcake Contest! I was so stoked to not only get a review copy of her book, but also to be the first stop on the virtual book tour!

When perusing Sweet Treats for a Sugar-Filled Life to decide what to bake for you for on the tour stop (what would a baking book tour be without sweet treats?), my choice was clear. In her book, Jessie creates the cupcake in a cupcake – genius!! The Everything Fall Cupcake is my own take on her creation (which, by the way, is her take on the work of her friend Megan Seling from Bake It In a Cake). If her cupcakes in cupcakes idea hadn’t existed, though, I would still have had many over-the-top outrageous recipes to choose from. In Jessie’s book, there are recipes for grilled cheesecake (two slices of pound cake with cheesecake in the middle), blondie-topped brownies (um, yum!), and the Pookie, a cookie-coated pie (that can’t be bad!). Grab a copy of the book now (or add it now to your holiday wish list) for tons of inspired recipe ideas or just to see more of Cuppie and friends.

To catch the rest of CakeSpy’s virtual tour, visit these blogs over the next two weeks:

More About Cupcakes In Cupcakes

When you bake a cupcake inside of a cupcake, you end up with a little cupcake nipple poking out of the top of the original cupcake. This is normal, and as you can see in the photo at the top of this post, once you frost the cupcakes, no one will ever know it was there.

Cupcakes inside of cupcakes open up a whole new realm of cupcake possibilities. Take any two cupcake and frosting flavors you love and you might love them even more in the same cupcake! Not only do you achieve different but complementary flavors in one bite, but you also end up with varied textures, a super moist center from the twice-baked cupcake, a typical cupcake texture from the normal-sized cupcake, and a top that has flaky crunchy bits from the mini-cupcake’s frosting spreading and caramelizing.

Warning: If you are one of those people who likes to keep all of their food groups separate on the plate (no peas touching the mashed potatoes), cupcakes in cupcakes are not for you.

How to Make The Everything Fall Cupcake

As I mentioned above, every component of these cupcakes has been featured on Cupcake Project before. So, rather than a recipe for the Everything Fall Cupcake, I’ve shared assembly instructions with you:

Bake mini apple cobbler cupcakes. To make the minis, chop the apple pieces a bit smaller than in the big cupcakes and cut the baking time down to fifteen minutes. You’ll end up with way more than you need if you follow the recipe exactly. If you don’t want a ton of extras (why wouldn’t you want extras, though?), cut the recipe in half.

I love the everything fall cupcake! But, I wanted to try something new, so I baked an apple cobbler mini cupcake with brown sugar frosting into a snickerdoodle cupcake and iced it with ultimate vanilla frosting. It was AMAZING!!

If I had the choice of baking two cupcakes together, I would have one as a pistachio cupcake….and the little one as a rocky road (chocolate, almonds, mini marshmallows). I would then frost with a light, fluffy white chocolate/marshmallow frosting….or instead of the marshmallow, almond sounds amazing. =) Sounds like a dream come true!!

Hi Stef! In your recipe for the Brown Sugar Frosting, you suggest using either light or dark sugar. Which one would you use for this particular recipe?? As always, thanks for sharing your amazing creations!

Your frosting and decoration on these cupcakes is gorgeous. So beautiful I couldn’t help myself and promised I would bake a batch of these for my friend that sent me a link here. Looking forward to trying them! Never thought of a cupcake inside a cupcake. Great idea!!!

I am kinda jealous at the way you have really got 4 seasons to inspire your cooking. We only get a coulpe of weeks tops for Fall in Australia and certainly don’t see quite the same colour change. Love the fun idea of a cupcake in a cupcake

I just baked a mini pecan pie cupcake inside a pumpkin cupcake and it tastes just like the pumpkin pecan cheesecake from the Cheesecake Factory! I didn’t frost the pecan pie cupcake, but I will frost the completed pumpkin pecan cupcake with brown sugar Swiss meringue buttercream. Mmmmm!

The apple cupcake came out a little dry for me. I think possibly I might have added a little too much baking powder. I would probably add more apples the next time to get a stronger flavor. Turned out really well putting them inside the pumpkin cupcake. I love the brulee effect the brown sugar frosting gives after baking. I love the brown sugar frosting! So good! Maybe even better than chocolate!

This was the best thanksgiving cupcake EVER! I could not get any rum for these cup cakes, but I made a very successful substitution. I added 1/4 tsp to 1/4 cup of apple juice to give it a caramel apple flavor. It was fantastic. I took one bite of this cupcake and time stood still, it was a life changing experience. Seriously, I am absolutely addicted to making cupcakes. I have never tasted anything more amazing in my life. This cupcake took time to make, but I have never even made a cake from scratch before this cupcake. So, if I can do it…anyone can.

I used honey crisp apples which made the apple cupcake sweeter and more moist. The recipe made 20 Everything Fall cupcakes and a few left over mini Apple cobbler cupcakes. I used light brown sugar and it was wonderful. I even added a little pumpkin spice marshmallow and dried cranberries for decoration. I am an incredible Cajun cook, but this was my first real attempt at baking, and I am absolutely sold on it now.

Stef, I absolutely LOVE your website. I live in New Zealand and am obsessed with cupcakes and bake at every opportunity! I made these cupcakes today. I made the apple yesterday, frosted and froze (the brown sugar frosting is Devine and whips up SO fluffy!).
I’ve just taken my Everything Fall cupcakes out of the oven and was a little disappointed. The recipe made 18 Everything Fall and then I had enough for six plain pumpkin rum and maple (which are so light, moist and fine crumbed!). Only 2 of the 18 Everything Fall cupcakes didn’t explode and leave a big sunken hardened caramel top.
I only lightly frosted the apple cobbler as I was worried about this. Devine recipe and I will absolutely make again, but I will just skip frosting the apple cobbler mini’s.
This is my first Cupcake Project recipe that I haven’t been 120% happy with, but others have had success, so it must just be me.